US3080434A - Process for producing aromatic compounds by pyrolysis - Google Patents
Process for producing aromatic compounds by pyrolysis Download PDFInfo
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- US3080434A US3080434A US780943A US78094358A US3080434A US 3080434 A US3080434 A US 3080434A US 780943 A US780943 A US 780943A US 78094358 A US78094358 A US 78094358A US 3080434 A US3080434 A US 3080434A
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- toluene
- bibenzyl
- temperature
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- 238000000034 method Methods 0.000 title claims description 10
- 150000001491 aromatic compounds Chemical class 0.000 title claims description 7
- 238000000197 pyrolysis Methods 0.000 title 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 54
- 238000006243 chemical reaction Methods 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 15
- 239000007858 starting material Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- -1 aromatic radical Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 150000003738 xylenes Chemical class 0.000 description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical compound CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 2
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 2
- HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 description 1
- TUIQGWQRVMJCAK-UHFFFAOYSA-N 1,3,5-trimethyl-2-[2-(2,4,6-trimethylphenyl)ethyl]benzene Chemical compound CC1=CC(C)=CC(C)=C1CCC1=C(C)C=C(C)C=C1C TUIQGWQRVMJCAK-UHFFFAOYSA-N 0.000 description 1
- OJGSITVFPMSVGU-UHFFFAOYSA-N 1-(2-naphthalen-1-ylethyl)naphthalene Chemical compound C1=CC=C2C(CCC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 OJGSITVFPMSVGU-UHFFFAOYSA-N 0.000 description 1
- BAVMXDNHWGQCSR-UHFFFAOYSA-N 1-[2-(2,3-dimethylphenyl)ethyl]-2,3-dimethylbenzene Chemical compound CC1=CC=CC(CCC=2C(=C(C)C=CC=2)C)=C1C BAVMXDNHWGQCSR-UHFFFAOYSA-N 0.000 description 1
- HHRXQMMXINWQCR-UHFFFAOYSA-N 1-ethyl-4-[2-(4-ethylphenyl)ethyl]benzene Chemical group C1=CC(CC)=CC=C1CCC1=CC=C(CC)C=C1 HHRXQMMXINWQCR-UHFFFAOYSA-N 0.000 description 1
- QFEPNMCDSBNJDB-UHFFFAOYSA-N 1-methyl-2-[2-(2-methylphenyl)ethyl]benzene Chemical compound CC1=CC=CC=C1CCC1=CC=CC=C1C QFEPNMCDSBNJDB-UHFFFAOYSA-N 0.000 description 1
- GBGPVUAOTCNZPT-UHFFFAOYSA-N 2-Methylcumarone Chemical compound C1=CC=C2OC(C)=CC2=C1 GBGPVUAOTCNZPT-UHFFFAOYSA-N 0.000 description 1
- IJPKSYDIENVRQO-UHFFFAOYSA-N 2-[2-(furan-2-yl)ethyl]furan Chemical compound C=1C=COC=1CCC1=CC=CO1 IJPKSYDIENVRQO-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- YUWFEBAXEOLKSG-UHFFFAOYSA-N hexamethylbenzene Chemical compound CC1=C(C)C(C)=C(C)C(C)=C1C YUWFEBAXEOLKSG-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001806 thionaphthenyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/76—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
Definitions
- X can be an aromatic radical of phenyl, indenyl, furanyl, pyrazyl, thiophenyl, benzofuranyl, thionaphthenyl, decalyl, etc.
- Y can be an alkyl radical having, for example, from one to 16 carbon atoms, such as methyl, ethyl, isopropyl, normal butyl, isobutyl, nor- 'mal pentyl, isopentyl, normal hexyl, isohexyl dodecyl cetyl, etc.; NH -NHR, wherein R can be X as defined above, or substituted derivatives thereof, or an alkyl radical having from one to 16 carbon atom
- R and R can be the same or different, but similar to R immediately above.
- Y can be CH A, where A can be phenyl, a substituted phenyl, etc.
- the substituent Y can be located on any available position on the aromatic ring.
- Examples of compounds which can be used include toluene, o,m,p-xylene, mesitylene, durene, isodurene, hexamethylbenzene, aniline, methylaniline, acetanilide, indene, methylthiophene, quinaldine, methylpyrazine, methylfuran, methylpyrolle, methylpyridine, or and fl-methylnaphthalene, methylbenzofuran, methylthianaphthene, m'ethyldecahydronaphthalene, etc.
- the aromatic compounds defined above can be used in admixture with each other but preferably are employed alone as the charge stock for the process of this invention.
- the charge stock is treated at an extremely high temperature, a low pressure and a carefully controlled contact time.
- the temperature must be sufliciently high to allow rupture between a terminal carbon on the substituen-t forming a part of the starting material and an adjacent hydrogen but not so high that coke formation is the predominant reaction.
- toluene is the starting material
- the temperature must be sufficiently high to cause rupture between the carbon on the methyl substituent and one of the hydrogens attached thereto.
- the benzyl thus obtained combines with another benzyl radical similarly obtained and bibenzyl is immediately formed.
- Example I 0.2601 mole of toluene, which was at 30 C. and 0.6 mm. Hg absolute, was passed through a reactor maintained at a temperature of 850 C. at such a rate that a contact time of 0.006 second was achieved.
- Example 11 Example III Similarly 0.3858 mole of toluene, which was at 30 C. and 1.1 mm. Hg absolute, was passed through a reactor maintained at a temperature of 925 C. at such a rate that a contact time of 0.0084 second was achieved. The product obtained was found to contain 0.0032 mole of bibenzyl, 0.3775 mole of toluene, 0.0015 mole of xylenes and 0.0004 mole of benzene. Efficiency of conversion to bibenzyl thus was 77.2.
- Example IV 0.3381 mole of toluene, which was at 30 C. and 0.8 mm. Hg absolute, was passed through a reactor maintained at a temperature of 850 C. at such a rate that a contact time of 0.0095 second was achieved. Obtained in the reaction product were 0.0016 mole of bibenzyl, 0.3339 mole of toluene, 0.0007 mole of xylenes and 0.0003 mole of benzene. The efliciency of conversion to bibenzyl was therefore 762.
- Example V Again 0.1961 mole of toluene, which was at 30 C. and 1.0 mm. Hg absolute, was passed through a reactor maintained at a temperature of 925 C. at such a rate that a contact time of 0.0138 second was achieved. The product obtained was found to have present 0.0013
- Example VI Similarly 0.1126 mole of toluene, which was at 30 C. and 2.5 mm. Hg. absolute, was passed through a reactor maintained at a temperature of 1000" C. at such a rate that a contact time of 0.0435 second was achieved. In the product obtained was found 00013 mole of bibenzyl, 0.0896 mole of toluene, 0.0016 mole of styrene, 0.0010 mole of xylenes and 0.0133 mole of benzene. Efliciency of conversion to bibenzyl was thus only 11.3.
- bibenzyl using toluene as starting material
- compounds which can be obtained from the starting materials defined hereinabove are bibenzyl, 1,2-ditolylethane, 1,2-dixylylethane, 1,2-dimesitylethane, 1,1,2,2-tetramethyl-1,2-diphenylethane, hydrazobenzene, 4,4'-diethylbibenzyl, ane, 1,2-dipyridy1ethane, 1,2-difuranylethane, 1,2-dinaphthylethane, 1,2-dipyrazylethane, hydrazotoluenes, etc.
- aromatic compounds obtained in the process can be used as heat exchange media, lubricating oils, chemical intermediates, etc.
- Bibenzyl for example, can be treated in accordance with the process disclosed and 1,2-dithiophenylethclaimed in our copending application Serial No. 780,949, filed concurrently herewith to obtain styrene and benzene.
- a process for producing aromatic compounds which comprises passing toluene through a reaction zone maintained at a temperature of about 800 to about 1200 C. at such a rate that a contact time of about 0.001 to about 0.015 second is achieved.
- a process for producing aromatic compounds which comprises passing toluene through a reaction zone maintained at a temperature of about 900 to about 1200 C.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Sites 3,000,434 PROCESS FOR PRQDUCING AROMATIC CQMPOUNDS BY PYRGLYSIS Raymond C. Odioso, Glenshaw, Pa, and Kenneth J.
Frech, Kent, Ohio, assiguors to Gulf Research & Development Company, Pittsburgh, Pa, a corporation of Delaware No Drawing. Filed Dec. 17, 1958, Ser. No. 780,943 2 Claims. (Cl. 260-670) wherein X can be an aromatic radical of phenyl, indenyl, furanyl, pyrazyl, thiophenyl, benzofuranyl, thionaphthenyl, decalyl, etc.; and Y can be an alkyl radical having, for example, from one to 16 carbon atoms, such as methyl, ethyl, isopropyl, normal butyl, isobutyl, nor- 'mal pentyl, isopentyl, normal hexyl, isohexyl dodecyl cetyl, etc.; NH -NHR, wherein R can be X as defined above, or substituted derivatives thereof, or an alkyl radical having from one to 16 carbon atoms, such as methyl, ethyl, isobutyl, hexyl, cetyl, etc.;
R! wherein R and R, can be the same or different, but similar to R immediately above. Similarly Y can be CH A, where A can be phenyl, a substituted phenyl, etc. The substituent Y can be located on any available position on the aromatic ring. Examples of compounds which can be used include toluene, o,m,p-xylene, mesitylene, durene, isodurene, hexamethylbenzene, aniline, methylaniline, acetanilide, indene, methylthiophene, quinaldine, methylpyrazine, methylfuran, methylpyrolle, methylpyridine, or and fl-methylnaphthalene, methylbenzofuran, methylthianaphthene, m'ethyldecahydronaphthalene, etc.
The aromatic compounds defined above can be used in admixture with each other but preferably are employed alone as the charge stock for the process of this invention. The charge stock is treated at an extremely high temperature, a low pressure and a carefully controlled contact time. The temperature must be sufliciently high to allow rupture between a terminal carbon on the substituen-t forming a part of the starting material and an adjacent hydrogen but not so high that coke formation is the predominant reaction. For example, in the case wherein toluene is the starting material, the temperature must be sufficiently high to cause rupture between the carbon on the methyl substituent and one of the hydrogens attached thereto. The benzyl thus obtained combines with another benzyl radical similarly obtained and bibenzyl is immediately formed. Thus it is absoare t 3,080,434 Patented Mar. 5, 1963 lutely necessary in the practice of this invention to pass the charge through a reaction zone maintained at a temperature of at least about 800, preferably about 900 to about 1200 C. The charge to the reaction zone can be preheated to any temperature below which thermal cracking of the charge is initiated. Although the threshold cracking temperature will vary with the charge stock employed, the preferred range of temperature will be in the range of about 20 to about 400 C. The pressure must be sufficiently low to permit and accelerate the rupture defined above and the inter molecular recombination to occur. Therefore a pressure of at least about 0.1 mm. Hg absolute, preferably from about 0.1 mm. Hg absolute to about atmospheric will sufiice.
Extremely critical in the practice of this invention is the contact time. We have found that in order to obtain a high conversion of the charge or starting material to the product aromatic compound it is absolutely necessary that the starting material hereinabove defined be maintained at the selected temperature for about 0.001 to about 0.015, preferably about 0.005 to about 0.008, second.
The process of this invention can further be illustrated by reference to the following examples.
Example I 0.2601 mole of toluene, which was at 30 C. and 0.6 mm. Hg absolute, Was passed through a reactor maintained at a temperature of 850 C. at such a rate that a contact time of 0.006 second was achieved. The
products obtained were analyzed by mass spectrometric and infrared procedures, and found to contain 0.0018 mole of bibenzyl, 0.256 mole of toluene, 0.0006 mole of xylene, and no benzene. Efliciency of conversion to bibenzyl was therefore 85.8 percent.
Example 11 Example III Similarly 0.3858 mole of toluene, which was at 30 C. and 1.1 mm. Hg absolute, was passed through a reactor maintained at a temperature of 925 C. at such a rate that a contact time of 0.0084 second was achieved. The product obtained was found to contain 0.0032 mole of bibenzyl, 0.3775 mole of toluene, 0.0015 mole of xylenes and 0.0004 mole of benzene. Efficiency of conversion to bibenzyl thus was 77.2.
Example IV 0.3381 mole of toluene, which was at 30 C. and 0.8 mm. Hg absolute, was passed through a reactor maintained at a temperature of 850 C. at such a rate that a contact time of 0.0095 second was achieved. Obtained in the reaction product were 0.0016 mole of bibenzyl, 0.3339 mole of toluene, 0.0007 mole of xylenes and 0.0003 mole of benzene. The efliciency of conversion to bibenzyl was therefore 762.
Example V Again 0.1961 mole of toluene, which was at 30 C. and 1.0 mm. Hg absolute, was passed through a reactor maintained at a temperature of 925 C. at such a rate that a contact time of 0.0138 second was achieved. The product obtained was found to have present 0.0013
invention is apparent from the above examples.
mole of bibenzyl, 0.1921 mole of toluene, 0.002 mole of xylenes and 0.0010 mole of benzene. Efliciency of conversion to bibenzyl was therefore 65.0.
Example VI Similarly 0.1126 mole of toluene, which was at 30 C. and 2.5 mm. Hg. absolute, was passed through a reactor maintained at a temperature of 1000" C. at such a rate that a contact time of 0.0435 second was achieved. In the product obtained was found 00013 mole of bibenzyl, 0.0896 mole of toluene, 0.0016 mole of styrene, 0.0010 mole of xylenes and 0.0133 mole of benzene. Efliciency of conversion to bibenzyl was thus only 11.3.
The criticality of contact time in the practice of our Note that as long as the contact time was maintained below 0.014 second, the efficiency of conversion to bibenzyl was high. Intact the lower the contact time the greater the efficiency. When the contact time was raised above 0.014 second, the efiiciency of conversion was reduced drastically.
While we have shown above the formation of bibenzyl using toluene as starting material, we can substitute any of the other compounds defined above as starting material in place of toluene to obtain the desired compounds. Examples of compounds which can be obtained from the starting materials defined hereinabove are bibenzyl, 1,2-ditolylethane, 1,2-dixylylethane, 1,2-dimesitylethane, 1,1,2,2-tetramethyl-1,2-diphenylethane, hydrazobenzene, 4,4'-diethylbibenzyl, ane, 1,2-dipyridy1ethane, 1,2-difuranylethane, 1,2-dinaphthylethane, 1,2-dipyrazylethane, hydrazotoluenes, etc.
The aromatic compounds obtained in the process can be used as heat exchange media, lubricating oils, chemical intermediates, etc. Bibenzyl, for example, can be treated in accordance with the process disclosed and 1,2-dithiophenylethclaimed in our copending application Serial No. 780,949, filed concurrently herewith to obtain styrene and benzene.
Obviously, many modifications and variations of the invention, as hereinabove set forth, can be made without departing from the spirit and scope thereof, and therefore only such limitations should be imposed as are indicated in the appended claims.
We claim:
1. A process for producing aromatic compounds which comprises passing toluene through a reaction zone maintained at a temperature of about 800 to about 1200 C. at such a rate that a contact time of about 0.001 to about 0.015 second is achieved.
2. A process for producing aromatic compounds which comprises passing toluene through a reaction zone maintained at a temperature of about 900 to about 1200 C.
at such a rate that a contact time of about 0.005 to about 0.008 second is achieved.
References Cited in the file of this patent UNITED STATES PATENTS 1,925,784 Williams Sept. 5, 1933 2,180,814 MattoX et a1. Nov. 21, 1939 2,208,517 Prutton June 16, 1940 2,767,057 Kennedy Oct. 16, 1956 FOREIGN PATENTS 581,046 Germany July 6, 1933 768,122 Great Britain Feb. 3, 1957 OTHER REFERENCES Szwarc, J. Chem. Phys., 16, pp. 128-136 (1948).
Genco et al.: The (CH) Bond Dissociation Energy in the Methyl Group of Toluene, United States Atomic Energy Commission. Publication ISC-746, March 1956 (36 pages).
Claims (1)
1. A PROCESS FOR PRODUCING AROMATIC COMPOUNDS WHICH COMPRISES PASSING TOLUENE THROUGH A REACTION ZONE MAINTAINED AT A TEMPERATURE OF ABOUT 800* TO ABOUT 1200*C. AT SUCH A RATE THAT A CONTACT TIME OF ABOUT 0.001 TO ABOUT 0.015 SECOND IS ACHIEVED.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US780943A US3080434A (en) | 1958-12-17 | 1958-12-17 | Process for producing aromatic compounds by pyrolysis |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US780943A US3080434A (en) | 1958-12-17 | 1958-12-17 | Process for producing aromatic compounds by pyrolysis |
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| Publication Number | Publication Date |
|---|---|
| US3080434A true US3080434A (en) | 1963-03-05 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US780943A Expired - Lifetime US3080434A (en) | 1958-12-17 | 1958-12-17 | Process for producing aromatic compounds by pyrolysis |
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| Country | Link |
|---|---|
| US (1) | US3080434A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3328473A (en) * | 1962-01-24 | 1967-06-27 | Monsanto Chemicals | Process for arylation of organic compounds |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE581046C (en) * | 1929-09-19 | 1933-07-20 | Fed Phosphorus Company | Process for the preparation of complex diaryl compounds of high boiling point |
| US1925784A (en) * | 1931-02-09 | 1933-09-05 | Dow Chemical Co | Process for making diphenyl |
| US2180814A (en) * | 1938-05-31 | 1939-11-21 | Universal Oil Prod Co | Manufacture of anthracene |
| US2208517A (en) * | 1935-07-20 | 1940-07-16 | Dow Chemical Co | Production of diaryl compounds |
| US2767057A (en) * | 1954-12-16 | 1956-10-16 | Sun Oil Co | Manufacture of hydrazine |
| GB768122A (en) * | 1953-02-06 | 1957-02-13 | Petrocarbon Ltd | Process for the production of polymers |
-
1958
- 1958-12-17 US US780943A patent/US3080434A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE581046C (en) * | 1929-09-19 | 1933-07-20 | Fed Phosphorus Company | Process for the preparation of complex diaryl compounds of high boiling point |
| US1925784A (en) * | 1931-02-09 | 1933-09-05 | Dow Chemical Co | Process for making diphenyl |
| US2208517A (en) * | 1935-07-20 | 1940-07-16 | Dow Chemical Co | Production of diaryl compounds |
| US2180814A (en) * | 1938-05-31 | 1939-11-21 | Universal Oil Prod Co | Manufacture of anthracene |
| GB768122A (en) * | 1953-02-06 | 1957-02-13 | Petrocarbon Ltd | Process for the production of polymers |
| US2767057A (en) * | 1954-12-16 | 1956-10-16 | Sun Oil Co | Manufacture of hydrazine |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3328473A (en) * | 1962-01-24 | 1967-06-27 | Monsanto Chemicals | Process for arylation of organic compounds |
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